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$101+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
gru 7 — gru 141
ndz. 12/7
ndz. 12/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in September or March, booked 43 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Find flight deals from O'Hare Intl to Portland

Cheapest flights from O'Hare Intl to Portland
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on Listopad 7, 2025.

This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pt. 11/2110:53 amORD - PWM
Nonstop2h 19mUnited Airlines
pon. 11/245:00 pmPWM - ORD
Nonstop2h 55mUnited Airlines
Deal found 11/6$249
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 12/66:04 amORD - PWM
1 stop4h 37mAmerican Airlines
wt. 12/95:34 amPWM - ORD
1 stop6h 21mAmerican Airlines
Deal found 11/5$251
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 12/117:40 amORD - PWM
2 stops24h 26mMultiple Airlines
sob. 1/106:18 pmPWM - ORD
1 stop25h 40mMultiple Airlines
Deal found 11/4$254
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 12/117:40 amORD - PWM
1 stop26h 01mMultiple Airlines
pon. 1/1211:29 amPWM - ORD
2 stops26h 01mMultiple Airlines
Deal found 11/4$258
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 11/198:30 amORD - PWM
1 stop5h 54mAmerican Airlines
wt. 12/25:21 pmPWM - ORD
1 stop4h 44mAmerican Airlines
Deal found 11/3$260
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 11/1810:53 amORD - PWM
Nonstop2h 19mUnited Airlines
wt. 11/256:00 amPWM - ORD
1 stop5h 45mUnited Airlines
Deal found 11/3$264
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 11/205:23 amORD - PWM
1 stop6h 07mDelta
śr. 12/36:00 amPWM - ORD
2 stops11h 42mDelta
Deal found 11/3$265
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pt. 12/1212:15 pmORD - PWM
1 stop28h 23mMultiple Airlines
pon. 12/156:05 pmPWM - ORD
2 stops18h 03mMultiple Airlines
Deal found 11/5$268
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pon. 11/177:15 amORD - PWM
1 stop5h 21mUnited Airlines
ndz. 12/144:25 pmPWM - ORD
Nonstop3h 10mUnited Airlines
Deal found 11/5$269
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pon. 11/172:35 pmORD - PWM
2 stops7h 44mDelta
śr. 12/36:00 amPWM - ORD
2 stops11h 42mDelta
Deal found 11/3$270
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 12/95:50 pmORD - PWM
Nonstop2h 27mUnited Airlines
ndz. 1/116:00 amPWM - ORD
1 stop5h 53mUnited Airlines
Deal found 11/4$273

Cheap flight deals from O'Hare Intl to Portland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated Listopad 7, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(United Airlines)

One-way from

$101
(Priceline)

Popular in

December

Cheapest in

September

Average price

$469

Good round-trip deal

$391 or less

Good one-way deal

$231 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Portland flights.
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From Chicago O'Hare Intl to Portland
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One-way flight from Chicago O'Hare Intl to Portland
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Highest demand for flights based on searches. 16% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated Listopad 7, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

O'Hare Intl

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

czw. 1/1

8:51 am-2:40 pm

1 stop4h 49m

Portland

sob. 1/10

8:40 am-1:15 pm

1 stop5h 35m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

śr. 1/28

9:54 am-3:31 pm

1 stop4h 37m

Portland

pon. 2/2

12:40 pm-6:34 pm

1 stop6h 54m

$260

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

pon. 12/8

12:35 pm-11:21 pm

1 stop9h 46m

Portland

pon. 1/12

5:30 am-1:39 pm

1 stop9h 09m

$269

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

wt. 11/18

10:46 am-11:54 pm

2 stops12h 08m

Portland

śr. 12/3

6:00 am-4:42 pm

2 stops11h 42m

$270

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

pt. 1/23

1:58 pm-12:20 am

2 stops9h 22m

Portland

ndz. 1/25

6:00 am-1:14 pm

1 stop8h 14m

$274

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

pt. 12/5

1:20 pm-10:23 pm

1 stop8h 03m

Portland

ndz. 12/7

6:08 am-2:59 pm

2 stops9h 51m

$284

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

wt. 11/18

6:15 pm-9:50 pm

Nonstop2h 35m

Portland

sob. 11/22

11:17 am-5:05 pm

1 stop6h 48m

$289

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

wt. 11/18

6:15 pm-9:50 pm

Nonstop2h 35m

Portland

wt. 12/2

4:25 pm-6:35 pm

Nonstop3h 10m

$299

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

śr. 11/19

10:53 am-2:12 pm

Nonstop2h 19m

Portland

śr. 12/3

4:25 pm-6:35 pm

Nonstop3h 10m

$299

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

pon. 11/17

6:15 pm-9:50 pm

Nonstop2h 35m

Portland

wt. 12/2

4:25 pm-6:35 pm

Nonstop3h 10m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 21 results
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Compare providers for flights from O'Hare Intl to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Portland in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Portland, Maine flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Portland

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Portland. Price data was last updated on October 31, 2025.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $71). Flying from Chicago O'Hare Intl Airport to Portland, Maine in February is currently the most expensive (average of $137). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to PWM?

Find hourly flight availability from O'Hare Intl to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated Listopad 7, 2025.

When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 15% versus a flight in the afternoon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated Listopad 7, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,007 reviews
Delta
7.9
Good
8,001 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,040 reviews
Delta
7.9
Good
8,001 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 6 inbound flights from Chicago O'Hare Intl per day. 3 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • How long is the flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Departing from Chicago O'Hare Intl Airport to Portland, Maine will take you 4h 37m. There are 897 mi between Chicago O'Hare Intl Airport and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Portland, Maine round-trip?

    According to our current data, Delta ($163), United Airlines ($226), and American Airlines ($232) offers the cheapest pricing from Chicago O'Hare Intl Airport to Portland, Maine. You may be able to fly from Chicago O'Hare Intl Airport to Portland, Maine for 59% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Portland, Maine?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Portland, Maine are Air New Zealand (85%), United Airlines (84%) and Republic Airways (83%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Portland, Maine?

    While on average a flight from Chicago O'Hare Intl Airport to Portland, Maine is generally $412, our data shows the cheapest flight currently is $165. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $209 for that flight.

  • Can I find deals for flights from O'Hare Intl to Portland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Portland.

  • Can I find deals for business class flights from O'Hare Intl to Portland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $71). Flying from Chicago O'Hare Intl Airport to Portland, Maine in February is currently the most expensive (average of $137). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Top 3 airlines flying from O'Hare Intl to Portland

Discover the top 3 airlines that operate flights from O'Hare Intl to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated Listopad 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$381FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$352FlexibilityNo cancel feeOn-time71%

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